EP0104432A2 - Herbizid und Pflanzenwachstumsregulator eine alpha-beta-ungesättigte Verbindung enthaltend - Google Patents

Herbizid und Pflanzenwachstumsregulator eine alpha-beta-ungesättigte Verbindung enthaltend Download PDF

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Publication number
EP0104432A2
EP0104432A2 EP83108306A EP83108306A EP0104432A2 EP 0104432 A2 EP0104432 A2 EP 0104432A2 EP 83108306 A EP83108306 A EP 83108306A EP 83108306 A EP83108306 A EP 83108306A EP 0104432 A2 EP0104432 A2 EP 0104432A2
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Prior art keywords
group
formula
alkyl
phenyl
groups
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English (en)
French (fr)
Inventor
Toshiyuki Hiramatsu
Shizuo Azuma
Teizo Yamaji
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Teijin Ltd
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Teijin Ltd
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Priority claimed from JP14627682A external-priority patent/JPS5951202A/ja
Priority claimed from JP17783A external-priority patent/JPS59128305A/ja
Application filed by Teijin Ltd filed Critical Teijin Ltd
Publication of EP0104432A2 publication Critical patent/EP0104432A2/de
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/02—Acyclic compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
    • A01N33/18—Nitro compounds
    • A01N33/20—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/30—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/48—Nitro-carboxylic acids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/50—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton

Definitions

  • This invention relates to a herbicide and a plant growth regulator which comprises an ⁇ , ⁇ -unsaturated compound as an active ingredient.
  • ⁇ , ⁇ -unsaturated compounds can be the active ingredients of herbicides.
  • ⁇ , ⁇ -unsaturated compounds are represented by the following formula We will describe below those ⁇ , ⁇ -unsaturated compounds which have been-known to be herbicidally active.
  • ⁇ , ⁇ -Unsaturated compounds of the formula in which the groups A and B bonded to the carbon atom at the ⁇ -position are bonded to each other to form a heterocyclic ring containing a nitrogen atom, or a sulfur atom or both are disclosed in U. S. Patents Nos. 3429895, 3634443, 3772331, 4020061 and 4052411 and Japanese Laid-Open Patent Publication No. 123,826/1975.
  • a,B-Unsaturated compounds of the formula in which the groups A and B bonded to the carbon-atom at the ⁇ -position are both mercapto or lower alkylthio groups are disclosed in Japanese Patent Publication No. 21,120/1970.
  • ⁇ , ⁇ -Unsaturated compounds of the formula in which one of the groups A and B bonded to the carbon atom at the ⁇ -position is a halogen atom and the other is a halogen atom, a substituted mercapto group, an amino group, a substituted amino group or a heterocyclic ring are disclosed in U. S. Patent No. 3590068.
  • ⁇ . ⁇ -Unsaturated compounds of the formula in which either one of the groups (D and E) bonded to the carbon atom at the a-position is a substituted phenyl ether are disclosed in Japanese Laid-Open Patent Publication No. 139,622/1976.
  • a,B-Unsaturated carboxylic acid esters of the formula in which either one of the groups (D and E) bonded to the carbon atom at the a-position is an aminoalkyl ester residue are disclosed in west German Patents Nos. 1,224,320 and 1,247,321.
  • U. S. Patent No. 3442638 discloses ⁇ , ⁇ -unsaturated carboxylic acid esters of the formula in which either one of the groups (D and E) bonded to the carbon atom at the a-position is an ester residue containing a mercury atom.
  • Another object of this invention is to provide a herbicide comprising as an active ingredient an a,$- unsaturated compound having a chemical structure in which the carbon atom at the a-position does not have a hydrogen atom but has two specified substituents.
  • Still another object of this invention is to provide a fast acting herbicide which when applied to the stalks or leaves of weeds, rapidly exhibits its herbicidal activity.
  • Still another object of this invention is to provide a herbicide having excellent absorbability which is very rapidly absorbed from the stalks or leaves of weeds, and with some types of its active ingredient, may begin to exhibit its herbicidal activity within 1 to 2 days after application.
  • Yet another object of this invention is to provide a herbicide having low animal and fish toxicity.
  • a further object of this invention is to provide a herbicide which exhibits excellent herbicidal activity against annual weeds.
  • a still further object of this invention is to provide a herbicide which exhibits excellent herbicidal activity against perennial weeds as well as annual weeds.
  • a yet further object of this invention is to provide a herbicide having excellent selectivity which exhibits strong herbicidal activity against either one of an annual broad-leaved weed and an annual narrow-leaved weed.
  • An additional object of this invention is to provide a herbicide which can be produced very easily at low cost.
  • a herbicide comprising as an active ingredient a,S-unsaturated compound represented by the following formula (I) wherein
  • the a,B-unsaturated compound used as an active ingredient-in this invention is represented by the above formula (I).
  • R 1 and R 2 may be identical or different.
  • the halogen atom is, for example, fluorine, chlorine or bromine, and chlorine or bromine is preferred.
  • the C 1-25 al k ox y and C 1-25 alkylthio groups may be linear or branched.
  • Examples of the C 1-25 alkoxy group include methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy, tert-butoxy, n-pentoxy, n-hexoxy, n-octoxy, n-nonanoxy, n-decanoxy, n-undecanoxy, n-dodecanoxy, n-stearyloxy, n-eicosanoxy and n-penta- cosanoxy.
  • alkoxy groups having 1 to 10 carbon atoms are preferred, and those having 1 to 8 carbon atoms are especially preferred.
  • Examples of the C 1-25 alkylthio groups include methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, sec-butylthio, iso-butylthio, tert-butylthio, n-pentylthio, n-hexylthio, n-octyl- thio, n-nonylthio, n-decylthio, n-undecylthio, n-dodecyl- thio, n-stearylthio, n-eicosylthio, and n-pentacosylthio.
  • alkylthio groups having 1 to 18 carbon atoms are preferred, and those having 1 to 10 carbon atoms are especially preferred.
  • the group (wherein Z 1 represents a C 1-25 alkyl group or a phenyl group, and the phenyl group may be substituted by 1 to 5 halogen atoms or 1 to 5 C 1-5 alkyl groups) represents alkyl or .phenyl.
  • alkyl includes acetyl, propionyl, butyryl, valeryl, caproyl, enathyl, caprilyl, pelargonyl, capryl, undecylyl, lauroyl, tridecanoyl, myristyl, pentadecanoyl, palmitoyl, margaryl, stearoyl, arachidyl, behenyl, and pentacosanoyl.
  • alkyl groups are preferred, and those having 1 to 11 carbon atoms in the alkyl moiety are especially preferred.
  • the halogen atom which can substitute the phenyl moiety of -C.phenyl is, for example, fluorine, chlorine O or bromine, and fluorine and chlorine are preferred.
  • the C 1-5 alkyl substituent is, for example, methyl, ethyl, propyl, butyl or pentyl.
  • phenyl examples include phenylcarbonyl, tolylcarbonyl, dimethylphenylcarbonyl, monoethylphenylcarbonyl, diethylphenylcarbonyl, isopropyl- phenylcarbonyl, tert-butylphenylcarbonyl, pentylphenyl- carbonyl, monochlorophenylcarbonyl, monobromophenyl- carbonyl, dichlorophenylcarbonyl, dibromophenylcarbonyl, trichlorophenylcarbonyl, 2-chloro-4-methylphenylcarbonyl, 2-bromo-4-methylphenylcarbonyl and 2-methyl-4-bromophenyl- carbonyl.
  • phenylcarbonyl mono- or di-halo- phenylcarbonyls, and monohalo-substituted mono-C 1-3 alkylsubstituted phenylcarbonyls are preferred.
  • Examples of one equivalent of a cation include an alkali metal such as sodium or potassium, 1/2 equivalent of an alkalin earth metal such as magnesium, calcium or barium, and ammonium ion of the following formula + NH( R )3 wherein R's, independently from each other, represent a hydrogen atom, a linear or branched alkyl group having 1 to 18 carbon atoms, preferably an alkyl group having 1 to l4.carbon atoms, a 5- or 6-membere
  • the C 1-25 alkyl group may be linear or branched, and includes, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, sec-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-hexadecyl, n-stearyl, n-eicosyl, n-heneicosyl and pentacosyl.
  • alkyl groups having 1 to 20 carbon atoms are preferred, and those having 1 to 15 carbon atoms are more preferred. Those having 1 to 10 carbon atoms are especially preferred.
  • phenyl(C 1-25 alkyl) groups examples include benzyl, a-phenethyl, ⁇ -phenethyl, 1-phenylpropyl, 2-phenylpropyl, 1-phenylbutyl, 1-phenyldecyl, 1-phenyl- dodecyl, 1-phenylstearyl, 1-phenyleicosyl, and 1-phenyl- pentadecyl. Of these, phenyl(C 1-12 alkyl) groups are preferred.
  • Z 2 represents a hydrogen atom, one equivalent of a cation or a C 1-25 alkyl group
  • preferred examples of the group are a carboxyl group, -COO.C 1-10 alkyl, ⁇ C 1-12 alkyl
  • Examples of the group in which Z 2 is a phenyl or phenyl(C 1-25 alkyl) group include phenoxycarbonyl, benzyloxycarbonyl, monochlorobenzyloxycarbonyl, dichlorobenzyloxycarbonyl, monobromobenzyloxycarbonyl, dibromobenzyloxycarbonyl, a-phenethyl-oxycarbonyl, ⁇ -phenethyloxycarbonyl, 1-phenylpropyloxycarbonyl, 3-phenylpropyloxycarbonyl, ⁇ -phenyldecyloxycarbonyl, ⁇ -phenyldodecyloxycarbonyl, ⁇ -phenylstearyloxycarbonyl and
  • phenoxycarbonyl and phenyl(C 1-18 alkyl)oxycarbonyl groups are preferred, and phenoxycarbonyl and phenyl(C 1-12 alkyl)oxycarbonyl groups are especially preferred.
  • the phenyl(C 1-18 or C 1-12 alkyl)oxycarbonyl groups preferably have 1 to 5 halogen atoms as a substituent at the phenyl moiety.
  • Examples of the group are mercapto- carbonyl and its salts, (methylthio)carbonyl, (ethylthio)-carbonyl, (phenylthio)carbonyl and (benzylthio)carbonyl.
  • Examples of the group are hydroxy(thiocarbonyl) and its salts, methoxy(thiocarbonyl), ethoxy(thiocarbonyl), phenoxy(thiocarbonyl) and benzyloxy(thiocarbonyl).
  • Examples of are mercaptothiocarbonyl and its salts, methyldithiocarbonyl, ethyldithiocarbonyl, phenyldithio- carbonyl and benzyldithiocarbonyl.
  • the groups are preferred as the group
  • the group (wherein Z 3 and Z 4 , i nde- pendently from each other, represent a hydrogen atom, a C 1-25 alkyl group, a phenyl(C 1-25 alkyl) group or a tri- azoyl group, and the triazolyl group may be substituted by a C 1-5 alkyl group, a phenyl group or a C 2-5 carboacyl group, or Z 3 and Z 4 may be bonded to each other to form a 5- or 6-membered ring together with the nitrogen atom to which they are bonded and X is an oxygen or sulfur atom) includes groups of the formulae
  • Examples of the phenyl(C 1-25 alkyl) and C 1-25 alkyl groups represented by Z and Z may be the same as given hereinabove with regard to Z 2 .
  • Examples of the C 1-5 alkyl group which can be a substituent on the triazolyl group are methyl, ethyl, propyl, butyl and pentyl.
  • Examples of the C 2-5 carboacyl substituent are acetyl, propionyl, butyryl and valeryl.
  • the group include carbamoyl, monomethylcarbamoyl, dimethylcarbamoyl, mono- ethylcarbamoyl, diethylcarbamoyl, monopropylcarbamoyl, monoisobutylcarbamoyl, mono-sec-butylcarbamoyl, mono- pentylcarbamoyl, monodecylcarbanioyl, monolaurylcarbamoyl, monostearylcarbamoyl, monopentacosylcarbamoyl, benzylcarbamoyl, dibenzylcarbamoyl, a-phenethylcarbamoyl, ⁇ -phenethylcarbamoyl, ⁇ -phenyldecylcarbamoyl, ⁇ -phenyl- stearylcarbamoyl, ⁇ -phenylpentacosylcarbamo
  • carbamoyl those groups of the above formula in which Z 3 and Z 4 , independently from each other, are C 1-18 alkyl, particularly C1-12 alkyl, phenyl(C 1-18 alkyl), particularly phenyl(C1-12 alkyl), and triazolyl, and those groups of the above formula in which Z 3 and Z 4 are bonded to each other to form a pyrrolidine or piperidine ring together with the nitrogen atom to which they are bonded are preferred.
  • Examples of the group include thiocarbamoyl, monomethylthiocarbamoyl, dimethylthiocarbamoyl, monoethylthiocarbamoyl-, diethylthiocarbamoyl, monopropyl- thiocarbamoyl, monoisobutylthiocarbamoyl, mono-sec-butyl- thiocarbamoyl, monopentylthiocarbamoyl, monodecylthio- carbamoyl, monolaurylthiocarbamoyl, monostearylthiocarba- moyl, monopentacosylthiocarbamoyl.
  • benzylthiocarbamoyl dibenzylthiocarbamoyl, a-phenethylthiocarbamoyl, ⁇ -phenethylthiocarbamoyl, ⁇ -phenyldecylthiocarbamoyl, ⁇ -phenylstearylthiocarbamoyl, ⁇ -phenylpentacosylthiocarba- moyl, 1,2,4-triazol-3-ylthiocarbamoyl, 5-phenyl-1,2,4-tri- azol-3-ylthiocarbamoyl, 5-methyl-1,2,4-triazal-3-ylthio- carbamoyl, 5-acetyl-L,2,4-triazol-3-ylthiocarbamoyl, pyrrolidylthiocarbonyl, piperidinothiocarbonyl, and morpholinothiocarbonyl.
  • thiocarbamoyl those groups of the above formula in which Z 3 and Z 4 , i nde - p endentl y from each other, are C1-18 alkyl, particularly C 1-12 alkyl, phenyl(C 1-18 alkyl), particularly phenyl-(C 1-12 alkyl) and triazolyl, and those groups of the above formula in which Z 3 and Z 4 are bonded to each other to form a pyrrolidine or piperidine ring together with the nitrogen atom to which they are bonded.
  • the C 1-25 alkyl groups may be interrupted by -O-, -S- or -NZ 8 in which Z 8 is a hydrogen atom or a C 1-10 alkyl group.
  • R 1 and R 2 groups are CN. NO 2 . haloaen atoms, groups of the formula (in which Z and X are as defined, provided that at least one of the two X's is an oxygen atom) and groups of the formula (in which Z 3 and Z 4 are as defined above).
  • Rand R 2 do not simultaneously represent the same member of the class consisting of NO 2 , halogen atoms and groups of formula in which Z 2 is a hydrogen atom.
  • R 1 or R 2 may be bonded to R 4 to form an acid anhydride group of the formula
  • the acid anhydride group is also a preferred example in this invention.
  • Z 5 -X (in which Z 5 represents a hydrogen atom or a C 1-25 alkyl group and X is an oxygen or sulfur atom) represents a hydroxyl group, a C 1-25 alkyloxy group, a mercapto group or a C 1-25 alkylthio group.
  • Examples of the C 1-25 alkyl group may be the same as those given hereinabove.
  • Z 6 represents a hydrogen atom, one equivalent of a cation or a C 1-25 alkyl group
  • Z 6 represents a hydrogen atom, one equivalent of a cation or a C 1-25 alkyl group
  • a carboxylate group one equivalent of a cation.OOC-
  • an ester residue (C 1-25 alkyl ⁇ OOC-).
  • carboxylate group and the ester residue are self-evident from the specific examples of one equivalent of a cation and C 1-25 alkyl given hereinabove, and are not given herein to avoid duplication.
  • a carboxyl group C 1-10 alkyl.OOC-, C 1-12 alkyl- H3OOC and H4OOC are especially preferred as the group
  • the group (in which Z 7 represents a hydrogen atom or a C 1-25 alkyl group) represents an acyloxy group of the formula Examples of the C 1-25 alkyl group may be the same as those given hereinabove. Of these, ( is preferred, and is especially preferred.
  • phenyl moiety of phenylthio, phenyl(C 1-25 alkylthio) and phenyl(C 1-25 alkoxy) may be substituted by 1 to 5 halogen atoms or 1 to 5 C 1-5 alkyl groups.
  • phenyl(C 1-25 alkylthio) examples include benzylthio, a-phenethylthio, ⁇ -phenethylthio, 1-phenyldodecylthio, 2-phenylpropylthio, 1-phenylbutylthio, 1-phenylpentylthio, 1-phenyldecylthio, 1-phenyldodecyl- thio, 1-phenylstearylthio, 1-phenyleicosylthio and 1-phenylpentacosylthio. Of these, phenyl(C 1-5 alkylthio) groups are preferred.
  • phenyl moiety of the above phenylthio, phenyl(C 1-25 alkylthio) and phenyl(C 1-25 alkoxy) groups may be substituted by 1 to 5 halogen atoms such as fluorine, chlorine or bromine or 1 to 5 C l-5 alkyl groups such as methyl, ethyl, propyl, butyl or pentyl.
  • R 4 in formula (I) represents a hydrogen atom, a C 1-25 alkyl group, a 3- to 6-membered cycloalkyl group, a phenyl(C 1-25 alkyl) group, or the same group as defined for R 3 . Except the 3- to 6-membered cycloalkyl group, examples of the above groups for R 4 may be the same as those given hereinabove.
  • Examples of the 3- to 6-membered cycloalkyl group are cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Cyclopropyl and cyclohexyl, are preferred.
  • R 3 and R 4 may be bonded to each other to form a 5- or 6-membered carboxylic ring together with the carbon atom to which they are bonded.
  • Examples of such a carbocyclic ring are a cyclopentane ring, a cyclohexane ring, a 3,3-ethylenedioxy-5,5-dimethylcyclohexane ring, and a 3-oxo-5,5-dimethylcyclohexane ring.
  • the C 1-25 alkyl groups may be interrupted by -O-, -S- or -NZ (in which Z represents a hydrogen atom or a C 1-10 alkyl group). Examples of the C 1-25 alkyl interrupted by such a hetero atom will be understood from the following Examples.
  • R 3 is preferably the same as above, and R 4 is preferably a hydrogen atom, C 1-25 alkyl, Z 51 X- (in which Z 51 is C 1-25 alkyl, and X is as defined above), or phenyl(C 1-10 alk y lthio).
  • the C 1-25 alkyl may be interrupted by -O- or -S-, and R 3 and R do not simultaneously represent the group of the class consisting of C 1-25 alkylthio groups and phenyl(C 1-10 alkylthio) groups.
  • R 3 and R 4 are simultaneously H O or HOO C, or R 1 and R 2 simultaneously represent the group in which Z 2 is a hydrogen, the compounds of of formula (I) are unstable and at least cannot be isolated.
  • R 3 and R 4 simultaneously represent HS, C 1-25 alkylthio, phenyl(C 1-25 alkyl)thio, or alkyl
  • R 3 is HO- and R 4 is a hydrogen atom, or R 1 and R 2 simultaneously represent N0 2 , halogen or C 1-25 alkoxy or alkylthio, the compounds do not meet the objects of this invention because they have weak or insufficient herbicidal activity or their herbicidal activity is exhibited slowly.
  • preferred ⁇ , ⁇ -unsaturated compounds as herbicidally active ingredients are those of the following formula (I)-l wherein
  • Especially preferred a,B-unsaturated compounds of formula (I)-l are those in which R 2 represents CN, NO2, a halogen atom, a group of the formula (in which Z 2 and X are as defined above, provided that at least one of the two X's is an oxygen atom), or a group of the formula (in which Z 2 and Z 3 are as defined above), or R 2 may be bonded to R 3 or R 4 to form an acid anhydride group, provided that R 11 and R 2 do not simultaneously represent the same member of the class consisting of halogen atoms and -COOH.
  • ⁇ , ⁇ -unsaturated compounds of formula (I) (including formula (I)-I) are given below.
  • specific compounds are given in the order of R 2 being CN, NO 2 , halogen, C 1-25 alkoxy or alkylthio, for each example of R 1 .
  • R 3 and R 4 are shown in a proper sequence as above for each specific example of R 2 .
  • R 2 alkoxy or alkylthio
  • R 1 is a halogen atom
  • R 2 alkoxy, alkylthio or
  • R 1 is alkoxy or alkylthio and R 2 is
  • R 2 is carbalkoxy
  • R 1 and R 2 are (520) 2-ethoxymethylene malonic acid di-sec.butyl amide
  • the ⁇ , ⁇ -unsaturated compound of formula (I) can be produced by any one of the following methods according to specified groups of R 1 , R 2 , R 3 and R 4 . These methods are known per se.
  • a first method is a condensation reaction shown by the following scheme.
  • This method can give ⁇ , ⁇ -unsaturated compounds of formula (I) in which R 3 and R 4 represent a hydrogen atom, a C 1-25 alkyl group, a 3- to 6-membered cycloalkyl group or a phenyl(C 1-25 alkyl) group, or R 3 and R 4 are bonded to each other to form a 5- or 6-membered carbocyclic ring, and R 1 and R 2 represent CN, N0 2 ,
  • a second method is a condensation reaction shown by the following scheme.
  • This method'can give a,S-unsaturated compounds of general formula (I) in which R 3 represents a hydrogen atom, a C 1-25 alkyl group, a 3- to 6-membered cycloalkyl group or a phenyl(C 1-25 alkyl group, R 4 is Z 5 X, and R 1 and R 2 represent CN, N0 2 ,
  • a third method is a reaction shown by the following scheme.
  • the third'method can give a,B-unsaturated compounds (b) corresponding to general formula (I) in which R 1 is a halogen atom.
  • Alcoholysis (or thioalcoholysis) of the compounds of formula (b) or the compounds of formula (b') can give a,B-unsaturated compounds of formula (I) in which R 1 is an alkoxy or alkylthio group having 1 to 25 carbon atoms, or a,B-unsaturated compounds of formula (I) in which R 3 represents Z 5 X-, a phenyl(C 1-25 alkylthio) group or a phenylthio group.
  • a fourth method is the hydrolysis of the product obtained by the second method, which yields an ⁇ , ⁇ -unsaturated compound of formula (I) in which R 4 is HO or HS.
  • a fifth method is a method for producing compounds of formula (I) in which R 3 is or R 4 and R 2 are bonded to each other to form an acid anhydride group.
  • the a,B-unsaturated compounds represented by formula (I) show excellent herbicidal activity and are used for combating weeds.
  • the weeds herein denote useless or hazardous plants which grow in environments created by man such as paddies and upland farms after they have come into these environments from the surrounding nature.
  • Examples of the weeds include plants of the family Gramineae such as those of the genera Digitaria, Sorghum and Echinochloa; plants of the family Plant- aginaceae such as genus Plantago; plants of the family Cyperaceae such as those of the genus Cyperus; plants of the family Compositae such as those of the genus Erigeron: plants of the family Cruciferae such as Barbarae vulgaris and those of the genus Raphanus; plants of the family Solanaceae such as those of the genus Physalis; plants of the family Commelinaceae such as those of the genus Commelina; and plants of the family Leguminosae such as those of the genus Medicago.
  • plants of the family Gramineae such as those of the genera Digitaria, Sorghum and Echinochloa
  • plants of the family Plant- aginaceae such as genus Plantago
  • plants of the family Cyperaceae such as those
  • the active compounds in accordance with this invention greatly affect the growth of plants, and therefore can control the growth of plants when applied in amounts smaller than those normally used in controlling weeds although the amounts may vary depending upon the kinds of the active compounds.
  • the active compounds of this invention can be applied to weeds or their habitat at a rate of 10 g to 200 kg, preferably 50 to 100 kg, per hectare.
  • the active compounds of this invention may be used in usual types of formulations such as solutions, emulsifiable concentrates, suspensions, dusts, pastes, or granules. These formulations may be prepared by using one or more of various adjuvants, for example, solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, ammonium sulfate and urea; liquid carriers such as water, alcohols, dioxane, acetone, xylene, cyclohexane, methylnaphthalene and dimethylformamide; surface-active agents, emulsifiers, dispersants and stickers such as alkyl sulfates, alkylsulfonic acid salts, ligninsulfonic acid salts, polyoxyethylene glycol ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene sorbitan monoalkylates, and dinaphthylme
  • formulations may be prepared, for example, by mixing the active compound with a carrier and/or an emulsifier exemplified above.
  • the active compound of this invention can be present usually in an amount of 0.01 to 99% by weight, preferably 0.1 to 95% by weight, in such a formulation.
  • the active compound of this invention may be applied singly or as a mixture with another active compound or in each of the formulations exemplified above to plants by usual methods such as spraying, atomizing, scattering and dusting.
  • the active compounds of this invention are characterized by being rapidly absorbed from the stalks or leaves of weeds and rapidly exhibit their herbicidal activity or plant growth modifying activity.
  • the active compounds of this invention include those which exhibit excellent activity against annual weeds, those which exhibit excellent activity against parennial weeds as well as annual weeds, and those which exhibit selective strong activity against one of an annual broad-leaved weed and an annual narrow-leaved weed.
  • active compound No. 330 of this invention was added to 225 parts of a mixture of acetone and water (volume ratio 1:1), and 0.5 part of a nonionic surface-active agent (Sorpol-2680, a tradename) to prepare a solution.
  • a nonionic surface-active agent Sorpol-2680, a tradename
  • active compound No. 318 of this invention was added to 250 parts of water, and 0.5 part of a nonionic surface-active agent was added (Alsoap-30, a tradename) to prepare a solution.
  • a nonionic surface-active agent Alsoap-30, a tradename
  • Example 1 0.1 Part of active compound No. 324 of this invention, 0.87 part of bentonite and 0.03 part of a nonionic surface-active agent (Sorpol 800-A, a tradename) were fully mixed to form a wettable powder which was diluted with water to a predetermined concentration.
  • a nonionic surface-active agent Sorpol 800-A, a tradename
  • the active compounds of this invention indicated in Table 2 were formulated in accordance with the above Formulation Examples. Seeds of the weeds indicated in Table 2 were sown, and after emergence, grown for 2 to 3 weeks.
  • Example 3 In the same way as in Example 1, the active compounds shown in Table 3 were tested, and the results are shown in the same table. These active compounds qere found to exhibit activity against annual plants and perennial broad-leaved plants.
  • the active compounds indicated in Table 5 were tested in the same way as in Example 1, and the results are shown in the same table. These active compounds were found to exhibit activity against the annual narrow-leaved plant.
  • Upland farm soil was put in pots (10 cm x 10 cm), and seeds of annual fleabane were sown. When they grew to a height of 8 to 10 cm, 2 ml of a chemical prepared in accordance with the following formulation was sprayed onto the plants. Ten days after the spraying, the growth of the plants was measured by their height.
  • the active compounds of this invention show herbicidal activity and plant growth modifying activity against weeds as shown in Examples 1 to 6. These compounds are useful for controlling weeds which grow in areas where useful plants are cultivated. Table 7 below gives a list of the active compounds of this invention which do not substantially affect the growth of rice, radish, maize, cucumber and soybean which are useful crops.

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  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP83108306A 1982-08-25 1983-08-23 Herbizid und Pflanzenwachstumsregulator eine alpha-beta-ungesättigte Verbindung enthaltend Withdrawn EP0104432A2 (de)

Applications Claiming Priority (4)

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JP146276/82 1982-08-25
JP14627682A JPS5951202A (ja) 1982-08-25 1982-08-25 除草剤
JP17783A JPS59128305A (ja) 1983-01-06 1983-01-06 除草剤
JP177/83 1983-01-06

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0213892A2 (de) 1985-08-27 1987-03-11 Rohm And Haas Company Enole mit herbizider Wirkung
WO1989007890A1 (en) * 1988-02-26 1989-09-08 L. Givaudan & Cie Societe Anonyme Antimicrobial agents
WO1991011503A1 (en) * 1990-01-12 1991-08-08 The Dow Chemical Company Composition and use of substituted 3-thio-2-propynenitriles as an industrial antimicrobial
US5039702A (en) * 1988-02-26 1991-08-13 Givaudan Corporation Alpha-halo-β-(substituted)thioacrylonitriles and their use for inhibiting the growth of microorganisms
US5126349A (en) * 1990-01-12 1992-06-30 The Dow Chemical Company Composition and use of substituted 3-thio-2-propynenitriles as an industrial antimicrobial
US5157051A (en) * 1992-03-05 1992-10-20 The Dow Chemical Company Composition and use of 3-thiocyano-2-halo-2-propenenitriles as antimicrobial agents
US5198445A (en) * 1990-01-12 1993-03-30 The Dow Chemical Company Composition and use of substituted 3-thio-2-propynenitriles as industrial antimicrobials
US5206227A (en) * 1992-06-02 1993-04-27 The Dow Chemical Company Composition and use of phosphonic acid, (2-halo-2-cyanoethenyl)-dialkyl esters as antimicrobials
US7842832B2 (en) 2001-12-19 2010-11-30 Basf Se β-amino-α-cyanoacrylates and their use as herbicides
US7851411B2 (en) 2001-12-19 2010-12-14 Basf Se α-Cyanoacrylates

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0213892A2 (de) 1985-08-27 1987-03-11 Rohm And Haas Company Enole mit herbizider Wirkung
US4781750A (en) * 1985-08-27 1988-11-01 Rohm And Haas Company Herbicidally active enols
EP0213892A3 (en) * 1985-08-27 1989-01-18 Rohm And Haas Company Herbicidally active enols
AU635702B2 (en) * 1988-02-26 1993-04-01 Givaudan-Roure (International) Sa Antimicrobial beta-substituted alpha-halo-acrylonitriles
US5039702A (en) * 1988-02-26 1991-08-13 Givaudan Corporation Alpha-halo-β-(substituted)thioacrylonitriles and their use for inhibiting the growth of microorganisms
WO1989007890A1 (en) * 1988-02-26 1989-09-08 L. Givaudan & Cie Societe Anonyme Antimicrobial agents
WO1991011503A1 (en) * 1990-01-12 1991-08-08 The Dow Chemical Company Composition and use of substituted 3-thio-2-propynenitriles as an industrial antimicrobial
US5126349A (en) * 1990-01-12 1992-06-30 The Dow Chemical Company Composition and use of substituted 3-thio-2-propynenitriles as an industrial antimicrobial
US5198445A (en) * 1990-01-12 1993-03-30 The Dow Chemical Company Composition and use of substituted 3-thio-2-propynenitriles as industrial antimicrobials
US5157051A (en) * 1992-03-05 1992-10-20 The Dow Chemical Company Composition and use of 3-thiocyano-2-halo-2-propenenitriles as antimicrobial agents
US5206227A (en) * 1992-06-02 1993-04-27 The Dow Chemical Company Composition and use of phosphonic acid, (2-halo-2-cyanoethenyl)-dialkyl esters as antimicrobials
US7842832B2 (en) 2001-12-19 2010-11-30 Basf Se β-amino-α-cyanoacrylates and their use as herbicides
US7851411B2 (en) 2001-12-19 2010-12-14 Basf Se α-Cyanoacrylates

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